Phenoxyacetic Acid → 2-[N-n-propyl,N-2-(phenyloxy)ethylamino]-5-methoxytetralin

HRID 327587

Reaction equation

HRID 327587 reaction equation
[CH2:1]([NH:4][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:15][CH3:16])[CH2:6]1)[CH2:2][CH3:3].[O:17]([CH2:24][C:25](O)=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[B-][N+](C)(C)C>>[CH3:16][O:15][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[CH2:13][CH2:14][CH:5]([N:4]([CH2:25][CH2:24][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:1][CH2:2][CH3:3])[CH2:6]2

Participants

4

Reactant 3

HCID 19188Phenoxyacetic AcidHCID 6327651Borane,N-dimethylmethanamine (1:1)HCID 102425482-Propylamino-5-methoxytetralin

Product 1

HCID 152288502-[N-n-propyl,N-2-(phenyloxy)ethylamino]-5-methoxytetralin

Procedure

A mixture of (-)-2-(N-n-propylamino)-5-methoxytetralin (80 mg, 31.9 mmol; prepared according to J. Chem. Soc., 1965, pp 26-36), phenoxyacetic acid (166 mg, 109.4 mmol) and borane trimethylamine complex (80 mg, 109.4 mmol) was refluxed in xylenes overnight. The cooled reaction mixture was extracted with NaHCO3 and the organic layer was dried over MgSo4, filtered and concentrated. The resulting oil was subjected to flash chromatography (Silica: 9:1 pet ether/EtOAc) and product was isolated with characteristic peaks at: NMR (300 MHz, CDCl3); δ 7.3-6.6 (m, 8H), 4.0(t,2H), 3.7(S,3H), 3.1-2.5(m,9H), 2.1(m,1H), 1.7-1.4(m,3H) 0.9(t,3H).

Workup

  1. customThe cooled reaction mixture
  2. extractionwas extracted with NaHCO3
  3. customthe organic layer was dried over MgSo4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customproduct was isolated with characteristic peaks at: NMR (300 MHz, CDCl3); δ 7.3-6.6 (m, 8H), 4.0(t,2H), 3.7(S,3H), 3.1-2.5(m,9H), 2.1(m,1H), 1.7-1.4(m,3H) 0.9(t,3H)

Sources & evidence

ORD record
ord-d00fd4a5353845a58ddd8c8f0af6d863
Source dataset
uspto-grants-1993_12
Patent number
US05274003

Linked notes

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